How to Conquer a Key West Bar Crawl

When you’re in Key West and up for a challenge, don’t miss out on the Key West Cocktail Challenge. Order a specialty cocktail at each of the six Pat Croce and Company restaurants and bars, including the Half Shell Raw Bar, Turtle Kraals, Charlie Mac’s 404, the Green Parrot Bar, Island Dogs Bar and the Rum Barrel. Ask your server for a Cocktail Challenge map at your first stop and receive a punch at each location after sampling a signature beverage. Don’t forget to drink responsibly! Once you’ve conquered the Cocktail Challenge, ask for your complimentary Key West Cocktail Challenge shirt and wear your bragging rights wherever you go. Wondering how to make it to all 6 establishments? The Cocktail Challenge is designed for you to go at your own pace and in any order with no deadlines. If you’d like to do it all in one day, check out our suggested Cocktail Challenge walking route to get started!

Start the evening off at Charlie Mac’s 404, where you can sample the most succulent and smoky BBQ in the Southernmost City. Home of award-winning BBQ pork sliders, brisket and more, dig in to your meal and order Charlie Mac’s signature Huckleberry Lemonade to get your first Cocktail Challenge map punch. Charlie Mac’s offers happy hour specials on weekdays, so it doesn’t hurt to start your adventure early and take advantage of great deals on drinks and appetizers.

After you’ve eaten your fill, mosey on over to the iconic Green Parrot Bar, conveniently located right next door to Charlie Mac’s. Order the Green Parrot’s signature Root Beer Barrel, enjoy some of South Florida’s best live music and snack on free popcorn. Both Charlie Mac’s and the Green Parrot Bar are located off Duval Street, so you can avoid large crowds and mingle with locals. Don’t forget to get a map punch before you head to your next stop.

Stroll down Whitehead Street and make a right on Fleming Street to capture a group shot in front of the famous Mile Marker 0. Then, make your way to Island Dogs Bar. You can come as you are and take a seat on Island Dogs’ breezy front porch for people watching and relaxation. This is a great way to meet other Key West tourists as well as locals. Sip Island Dogs’ signature Key Lime Pie Martini for a uniquely Key West treat and listen to live music.

If you’re a sports fan, you’ll love the next stop on this Key West bar crawl. The Rum Barrel is home to the Southernmost Phillies and Florida Gators clubs, complete with big screen TVs, craft beers and delicious food. While you’re drinking the Rum Barrel’s signature drink, you can try your hand at the restaurant’s beer pong game machine or head upstairs to the Quarterdeck for live music and a great view of the island.

Finally, walk over to Key West’s historic seaport for the last 2 stops on the Key West Cocktail Challenge. Turtle Kraals features a tangy Key Lime Margarita, so be sure to have a taste and get yet another map punch. You can relax upstairs at Turtle Kraals’ intimate Tower Bar for the perfect view of the Key West sunset (if you get there early enough) and the picturesque historic seaport. The restaurant is famous for its fresh Peruvian ceviche as well as live turtle races every Monday and Friday at 6 pm.

The Half Shell Raw Bar is the final stop on the Key West Cocktail Challenge. Sample an Oyster Shooter and a dozen fresh oysters sourced daily from the Half Shell Fish Market right next door. Meet locals and discuss the day’s adventures. You might even gather some suggestions for more of the top things to do in Key West. In between all the fun, don’t forget to present your filled out map to receive your complimentary Key West Cocktail Challenge shirt! The Key West Cocktail Challenge is a great way to see Key West and have an authentic and unforgettable island experience. Cheers!